


You're The Boss

by gnimaerd



Category: Arrow (TV 2012)
Genre: F/M
Language: English
Status: Completed
Published: 2015-01-14
Updated: 2015-01-14
Packaged: 2018-03-07 14:13:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,465
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3175752
Author URL: https://archiveofourown.org/users/gnimaerd/pseuds/gnimaerd
Summary: <blockquote class="userstuff">
              <p>The INEVITABLE gigilo!AU you’ve all doubtlessly been waiting for. Felicity Smoak is the only billionaire 25 year old we know, and running her multi-million dollar tech company doesn’t leave her a whole lot of time to date. So she does the natural thing, gets drunk and calls a male prostitute who may or may not have been recommended to her by her lawyer at 3AM. Oliver Dearden: Professional Ladies Man, known in the business as The Arrow, turns up, and hilarity and orgasms ensue.</p>
            </blockquote>





	You're The Boss

**Author's Note:**

  * For [RosieTwiggs](https://archiveofourown.org/users/RosieTwiggs/gifts).



> this fic is dedicated to rosietwiggs who massively enabled me into writing it, damn her. Also, there may well be more of this at some point - I have a lot of other loosely connected scenes from this universe, I just need to find the time to thread them into something vaguely resembling a plot.

“Oh honey,” Laurel says, over lunch, “you need a holiday.”

 

Felicity snorts. “Me? Seriously? You think I have time for a break right now?”

  
“I didn't say you have time,” Laurel tosses her hair out of her eyes – she has really, ridiculously perfect hair, it's kind of unfair – Felicity makes a mental note to ask who does it for her, all the money she has she should definitely be able to afford to have hair as good as Laurel Lance, “just that you need one. Seriously, when was the last time you got more than four hours of sleep a night?”

 

Felicity doesn't answer that, because she doesn't want to experience another of Laurel's patented judgemental looks.

 

“Maybe she doesn't need a break,” Sara cuts in, reaching across the table for the very, very expensive fries that Felicity swears aren't as good as the kind she can get for  a dollar ninety at Big Belly, “maybe she just needs to get laid. When was the last time that happened, huh?”

 

She waggles her eyebrows at Felicity and Felicity doesn't answer that, either.

 

“Oh, honey,” Laurel sighs.

 

“Don't _oh honey_ me,” Felicity purses her lips, “I didn't get to be the only billionaire twenty five year old that you know so you could _oh honey_ me.”

 

“And yet, here I am – oh honey-ing,” Laurel shakes her head.

 

“I don't see you dating all that regularly either,” Felicity grimaces, “being my lawyer can't leave you that much more spare time than I have.”

 

“I don't need to date to have an orgasm,” Laurel replies, making her sister snort up coke all over herself – she hands Sara a napkin as she talks, “really, you're in the technology business, Felicity, you know we have machines to do that for us now, right?”

 

Sara has finished choking as she giggles, “this is so not what I want to hear my big sister discussing with her boss over lunch.”

 

“Felicity's your boss too.”

 

“Doesn't mean I'm paid enough to put up with this crap.”

 

“You're her bodyguard, Sara, you're paid to watch her pee but you can't deal with – ”

 

“ _She does not watch me pee_!” Felicity might have said that a little too loudly. She watches heads turn at the neighbouring table and takes a deep, hasty gulp of the really excellent red wine they're having with lunch. (This, she knows, she can't pay a dollar ninety for at Big Belly).

 

“Back on topic,” Laurel interupts, pushing that ridiculous hair back out of her eyes again, “you need a break, Felicity. Or an orgasm. Or both. Seriously, I'm worried about you.”

 

“I'm fine, Laurel.”

 

“You look exhausted. And thin – really thin – are you making sure she's eating?” This last is directed at Sara, who shrugs.

 

“Not my job.”

 

“Your job is to keep her safe – ”

 

“From bad guys, not her own shitty self-care,” Sara rolls her eyes, “I try, okay? But you know Felicity. She'd forget to shower if Digg didn't literally pick her up and put her in the bathroom a couple of times a week.”

 

“That happened one time,” Felicity folds her arms, “and in my defence, we were in the middle of that awful Palmer merger and I was very, very stressed.”

 

Laurel fixes Felicity with her judgemental eyebrows and Felicity grimaces.

 

The thing is, they both know her too well. The Lance sisters have been hanging around since she was a dorky  sixteen year old running her one-woman (...one-teenager) start-up out of her mom's kitchen, and Laurel, half way through law school at the time and looking for extra-credit, had been helping her get all her business licenses and contracts in order. Now there's a great big shiny sky-scraper in the middle of Starling City with _Smoak Inc_ picked out in neon-pink at the top (there's an outside chance that Felicity likes reminding her business rivals that they've been beaten to fuck by a girl, okay?) and Laurel's law firm is like 50% silently bank rolled by Felicity who likes making sure that Laurel always has funds to take on pro-bono cases.

 

It's been a hell of a nine years and there's a fair chance, too, that Laurel and Sara might be Felicity's best friends. And that Felicity tries not to think too much about the fact that she could buy herself a private island but her closest friends are her lawyer and her bodyguard and she could go days talking to literally no one but people she employs to talk to her – but.

 

“Felicity,” Laurel sighs, reaching over the table to take Felicity's hand, “I'm serious. I haven't seen you this bad since – well. The Palmer merger. Isn't there any way you can take a couple of days?”

 

Felicity snorts. “Yeah, no. We're acquiring Star Labs next week, a holiday is not going to happen to me any time soon.”

 

“All that money don't buy her spare time,” Sara shakes her head, sardonically, “could buy her like a yacht, or something, though.”

 

It could buy her a cruise ship, actually, but Felicity doesn't say that. “It's not that simple. I have responsibilities. Like, a lot of responsibilities.”

 

“Honey, we know,” Laurel assures her. “I just... really, I promise, you could have some time out without the company falling apart, you know that, right? The kind of money you've got on you now – you can afford some down time. And I think you may really need some down time. Look at your nails.”

 

It's true she can't remember the last time she had a manicure – Felicity looks at her fingernails and feels a moment of profound sadness over the state of her cuticals. She used to love manicures. Hell, Laurel was there for her first one, which Felicity paid for the first time they made a profit – her, her mom, Laurel and Sara in the plastic-smelling neon bright little nail salon next to the Big Belly Burger two blocks from her home. It had felt like the absolute frickin heights of luxury back then. And it's kind of been a thing, since then – it became a weekly occurrence the moment that Felicity could afford it to be – she really likes having her nails done, damn it.

 

And she literally cannot remember the last time she felt able to sit still long enough to sit through one.

 

“I just... even if I went away,” Felicity sighs, pinching the bridge of her nose, “I don't think I could relax. I would spend literally the whole time worrying. I don't need a break – I just – I need...” She lowers her voice, leaning across the table, “I would really, really like to have sex. Like good sex. It has been – far, far too long.”

 

To her credit, Laurel doesn't laugh at her – she pats Felicity's hand, gently.

 

Sara laughs at her, though it's not an unkind sound. She throws her head back, ruffles Felicity's hair affectionately. “I knew it. I knew she needed someone to like – screw her brains out.”

 

“That's classy, Sara.”

 

“I'm not judging her!” Sara waves a hand, “she just needs a nice young man to come along and – well. Come.”

 

“Sara!”

 

“Or a nice young woman, whatever, like I said I'm in no position to judge.”

 

“Sara,” Laurel glares at her, then blances back at Felicity – currently a colour seldom seen in nature – then sighs. “Look, if I said I knew someone who might be able to help you with that, would you be interested?”

 

Felicity blinks, “what do you mean?”

 

“I mean,” Laurel goes digging in her wallet, and then produces a business card, “I know a guy. Who might be able to help you out with that.”

 

“A – guy?” Felicity takes the card, staring at it for a moment.

 

“What kind of guy?” Sara sits up, “oh my god – Laurel – what kind of guy?”

 

“Let's say that sometimes the tech doesn't do it for me,” Laurel shrugs, nonchalantly, and Sara promptly collapses into disbelieving laughter.

 

“Oh my god. Oh my god. I am so telling dad.”

 

“You tell dad, I'll tell him what I caught you doing with that scary lady from the League.”

 

Sara snorts, “yeah, sure, give him a heart attack, that's on you.”

  
“Can I just – ” Felicity waves the card, pointedly, lowering her voice to a hiss, “is my lawyer seriously advising me to higher a – _prostitute_?”

 

“He's a male escort,” Laurel intones, in an entirely reasonable voice, like she's advising Felicity on contract law rather than a sex crime. “His name is Oliver, he's discreet, he's clean and he's very, very nice. And if you want to imbue yourself of his services, Felicity, I cannot recommend his work highly enough.”

 

“I... have no idea how to feel about this.”

 

“Feel grateful, and if you want to experience the best – oral work – of your life, call him.” Laurel taps the card, pointedly.

 

Felicity's eyebrows shoot up – Sara is still giggling.

 

“...seriously?”

 

“Oh yeah.”

 

“Oral – ”

 

“ _Oh yeah_.”

 

Felicity stares at the card – there's just a name – Oliver Dearden – and a number, an email address – and a little logo with an arrow, like the kind you'd use for archery. _Subtle,_ Felicity thinks, dryly.

 

 She pockets the card, and tells herself that she'll never use it.

 

***  


Holy wow this was a terrible idea. Half a bottle of red wine all on her own at three in the morning levels of terrible.

 

And in her defence she didn't expect Oliver Dearden to pick up his phone at that time of night, either. Sounding totally awake and smoothly professional, like a helpline operator or a personal assistant, not a – you know.

 

He promises to be over in half an hour and what do you know? He's right on time – although it's also enough time for Felicity to have sobered up significantly since deciding that calling him was in any way advisable. She has shaken Sara awake.

 

“I did something stupid!”

 

“Mm?” Sara blinks at her from the bed she occupies in the spare room – the spare wing, really – of Felicity's obscenely enormous penthouse apartment, “you realise you have a night shift security detail to handle this stuff for you, right?”

 

“But I can't tell them about this,” Felicity moans, clambering into bed next to her and hiding her face in Sara's shoulder, “this is so embarrassing, Sara, seriously, I can't believe I – please just go down there and make him go away.”

 

“You sure?” Sara asks, petting her, gently. “I mean, you called him for a reason, right? And Laurel's not gonna recommend someone who's like – a psycho, or something. What if he's nice? What if he's really, really that good at – the stuff I don't want to picture my sister doing.”

 

Felicity covers her face with her hands, whining softly.

 

“Okay, what if I go down, and check him out for you, and if he seems okay, I'll bring him back up here, and you can – interview him. Like for a job. You do that all the time, right?” Sara gives her a gentle prod in the ribs, “You can – assess his suitability, or whatever. Then maybe next time you're drunk and horny at three in the morning, you'll know if you actually want to have sex with him or if you're gonna end up hauling me out of bed to deal with the male hooker you called after having too much wine.”

 

Felicity puffs out her cheeks and then sighs, heavily. “Okay. Okay, let's do that.”

 

“Great,” Sara prods her again, “but I'm gonna need you to get off me now so I can put some clothes on. And you should, too. I mean, unless you want to meet this guy in your panda onesie, that's totally up to you, you're the billionaire here.”

 

Felicity puts some clothes on.

 

***  
  
Oliver is checking his watch when the short, wirey blond appears in the lobby of the expensive apartment building he's been called to. She's almost certainly not the one who called him – Oliver Queen has been in this business long enough to know a bodyguard when he meets one, it's all in her muscular forearms and loose, powerful strides – not ex-military, he'd guess, but she's seen combat somewhere.

 

“Oliver Dearden?” She offers a firm handshake, “you're coming with me. My employer wants to meet you.”

 

“Okay.”

 

She doesn't supply her name before she pats him down – he's used to this, the kind of clientele he deals with tend to have security concerns – she's brisk and efficient, though there's an appreciative glitter in her eyes that hints at the possibility she's enjoying running her small hands over him a little more than she should. (He's used to that, too).

 

“Right, you're good,” she smacks him on the ass and takes him over to a private elevator, which she opens with a key from a number hanging from a chain around her wrist.

 

He doesn't miss her checking him out again on the entirely silent elevator ride to the top floor of the building.

 

And the thing is, he's had rich clients. He's got a few really, obscenely wealthy women on his regulars list – but. He can smell the money coming off this place from the elevator and when he steps out, into the lobby of a penthouse that looks like it's made entirely of marble and glass, he knows he's wondered into the sort of wealth he hasn't encountered since his Bratva days.

 

“Through there,” the bodyguard directs him at an archway that looks like it leads into a drawing room – he can see a wide, modern fireplace, lit, and some very expensive looking minimalist furniture – then she grabs his arm, “you be nice, Mr Dearden, or I will break every bone in your body and then drop kick you off the roof, okay?”

 

Her tone is entirely calm and reasonable which is how Oliver knows this woman isn't kidding. He looks at the muscles in her arms and decides she could also probably do it, easily. He nods, and she lets him go.

 

But the thing is, he's really not expecting what he's confronted with once he gets into the drawing room.

 

Felicity Smoak is small, smaller than her bodyguard, looking a little pale and tired behind a pair of (designer? Designer) glasses, seated on the sofa with a tablet and a stack of papers, chewing a red pen.

 

She's young. She's really, really young. Oliver deals for the most part in women who are in their thirties and older – women who are his age and older. The odd rich girl occasionally mis-uses daddy's credit card to spend a night with him, but generally, regularly, it's women who have their own money and have worked half their lives to acquire it. This girl isn't out of her mid-twenties and the glasses and the pose make her look even younger – closer to Thea's age, Christ. Either she was born into this money or she's one of those crazy tech geniuses he hears about sometimes. Maybe she invented an app. That's a thing, right?

 

She looks up at him from behind her glasses and smiles in a way that shows only the edge of her nerves. “Hi.”

 

“Hi,” he turns on his best professional smile and sees her relax, just a little. “Miss Smoak?”

 

“Felicity,” she shifts a little, indicates the other end of the lengthy sofa, “sit down. Do you want something to drink? I can have Sara – ”

 

“I'm fine,” he promises. He doesn't drink on the job (or ever, these days, really – it’s a slippery slope he’d rather not end up on), and he's not about to sit here and have tea with this woman. That's kind of obviously not what she really wants.

 

“Um, so,” she shifts again, pulling her feet up under her and adjusting her tablet, “I was just gonna ask you some questions – if that's okay?”

 

“Sure,” he shrugs. “You wanna see my doctor's note?”

 

“What?”

 

He lays his briefcase down on the sofa – opens it away from her, so she won't see the condoms or the lubricants or the sex toys (he's a professional, he has his tools), and produces a thin file, which contains his medical history, and a certificate declaring him free of any infections.

 

“I get checked once a month,” he tells her, as he hands it to her, “and I always carry proof. I find it puts my clients at ease.”

 

She examines the file for a moment – this is all new to her, it has to be. She doesn't, at all, seem like someone who does this regularly – she's probably never even been to a strip joint before let alone come looking for an escort. God, she's young.

 

“Thank you,” she hands it back to him, “that's – um – reassuring. But I was wondering something else?”

 

“Whatever you wanna know,” he puts the file away, sits back – tries the professional smile again. But she's not buying it, somehow, he can tell. She's not willing to buy into the fiction that most of his clients do – the illusion of intimacy that they can buy themselves for a night (or a weekend or whatever their bank accounts will stretch to). That is really not who this girl is, and he's had clients who are like this, too – the ones who would rather dwell in the stark facts of the situation than let him seduce them into imagining there's any reality to their relationship beyond a business transaction – but they're rare and they're tricky – skittish. This will not be easy.

 

On the other hand, clients like this are usually pretty sane, fair, even easy going once they've relaxed – if they become regulars they're usually good tippers and they tend to be his easiest gigs, there's no need to pretend with them, and that makes some of what he does much easier.

 

“How long have you been – ” She's playing with a strand of hair. It's not helping the overall air of vulnerability hanging around her shoulders. “You know.”

 

“I've been in this business seven years or so,” he shrugs, “I was a dancer, before that.”

 

“Like – in a club?”

 

“I would take my clothes off whilst drunk women stuffed dollar bills in my g-string, yes.”

 

She giggles, nervously, ducking her head, then glances up at him again. “Why?”

 

“Why would they stuff dollar bills in my g-string?”

 

“No – I mean,” she flushes – he's only making her more uncomfortable, god how does he get her to relax? “why did you... start?”

 

“Good money,” he replies, truthfully – but she clearly wants more than that. She's trying to get at something, but he's not sure what she wants to hear. “The dancing was fewer hours and much, much better pay than I got being a waiter, or a barrista, or washing cars – all of which I was also doing at the time. The escorting was even better money so... natural career progression.” He shrugs, “and I get to choose my own clients and my own hours this way, that helps.”

 

“So you needed money?” She presses and ah – okay. That's what she's interested in.

 

Oliver studies her for a moment, trying to gauge how much he'll have to give away for her to feel able to trust him. He also gauges the wealth in the room, the odds of this woman being an extremely good tipper, the amount of rent he owes given how much of Thea's tuition he just had to pay and their washer-dryer needing fixed and the car needing its break lights replaced and –

 

Fuck it.

 

“When I was eighteen my parents were killed,” Oliver spreads his hands, gently, watching Felicity's eyebrows raise. “Car accident. I thought we had money – we had – you know – a pretty nice life when I was growing up. But it turns out dad had put us in a lot of debt and by the time he died we had pretty much nothing. The house had to be sold to clear the debt and after that there wasn't anything left for me or my sister. She was twelve years old. I dropped out of college to take care of her and try and figure out a way to keep a roof over our heads and it turns out – this has been it. Now she's in college, so I'm keeping at it to put her through school – I figure I'll stop once she graduates, but right now tuition doesn't pay for itself, so.”

 

Felicity nods, slowly – and finally, finally loses the line of tension running across her shoulders.

 

Oliver doesn't ordinarily tell that story. It's part of how he stays sane – he keeps his personal stuff out of his job, and he especially keeps Thea's name out of it – that's what lets him put on his professional mask, become Oliver Dearden, the Arrow, the professional ladies' man who always smells incredible and carries his medical history in a briefcase next to strawberry flavoured condoms and a vibrator. That story, the real one, belongs to Oliver Queen, the idiot kid who had to grow the fuck up pretty much over night or risk losing his sister to the foster care system – the guy who still proof-reads all her essays, sits up and waits for her to come home at night and background checks all her boyfriends. The guy who has a cat and a fern and bills to pay.

 

But Felicity clearly needs him to open up – needs some show of humanity if she's going to trust him with her own.

 

“Does she – know?” Felicity is watching him, her expression open, curious.

 

“What?”

 

“Your sister, does she know what you do?”

 

“No,” he shakes his head, tightly.

 

“Oh,” she frowns for a moment, “that's gotta be – not that fun, huh?”

 

He shrugs again. This is not how he pictured this encounter going down, at all, and now he's the uncomfortable one, great – he needs to steer this conversation back toward something he could actually get paid for. “Did you really call me over here just to ask me questions, Miss Smoak?”

 

“Well, I'm interviewing you,” she taps her tablet, pointedly.

 

“Interviewing me?”

 

“Yeah. Like for a job. I interview all my employees, pretty much. Certainly the ones I have to have contact with, I interview them all myself. My PA thinks I'm insane but I think that's what makes my business so successful.” She purses her lips and – damn, she's cute. “So, Mr Dearden, what makes you think you're suitable for the job of being my – ” she screws up her face for a moment (okay, yeah, really fucking cute). “I was gonna say 'lover' but that sounds awful no matter how you say it.”

 

He laughs, because he is momentarily genuinely charmed by her – and she smiles, and this feels less awkward now, so that's something. She’s cute and she must be fucking smart if all of this is really hers, and she seems grounded, thoughtful – normal. He could like her, he suspects, quite a lot.

 

So Oliver considers the question seriously for a moment, then spreads his hands.

 

“Okay,” he proffers, gently, “look, you strike me as the sort of woman who hasn't got a lot of spare time – someone who's accumulated all this... as young as you look – you must work pretty hard. So what you want isn't wining and dining and conversation – all of which, by the way, I can do – this,” he points at his face, “is not just a pretty package, okay, you can value me for my brain, too – ” She giggles – this is working, great, excellent, they're gonna get somewhere, “what you want, though, I'm gonna guess, is someone who will come by at three in the morning, quite potentially with pizza, and make you feel good, clean up after themselves and leave – quietly and without causing that terrifying woman you call a bodyguard to drop kick them off a roof. Am I on the right track here?”

 

Felicity smiles, ruefully. “Close enough. Although for future reference I prefer dim sum to pizza at three in the morning.”

 

“For future reference?”

 

“Well, you are kind of acing this interview so far.”

 

He grins at her – not his professional smile – and she smiles back and – fuck, she has dimples.

 

“Yeah – so all of that? I can totally do,” he shrugs, “dim sum and everything. Although I'm going to suggest that the only way you'll know if this is something you really want is if I demonstrate for you.”

 

He watches her ears turn pink – but she holds her nerve. “Demonstrate what?”

 

“Whatever you want,” he waves a hand, “totally up to you. And if you don't like any of it, you say stop and it all stops, instantly. You're the boss.”

 

Felicity chews her lip, then nods, slowly. “Oh – okay. Okay then – can – I look at you?”

 

“Aren't you already?”

 

“I mean – without your shirt,” she folds her arms, a little defensively – her ears are still pink but her eyes are bright, her lips twitching into the hint of a smile. “And also... potentially without your pants...”

 

He grins. “You can do that. Here, or in your bedroom?”

 

“Bedroom. Please.”

 

“For future reference, you don't have to say please.”

 

***  


Oh wow this man is like – walking photoshop. Or something. Seriously. What _– the fuck_.

 

Felicity tries really hard not to stare but then – well she has kind of paid to look at this artwork of a human being. Wow. _Wow._

 

“Are those…” she sits cross legged on the end of her bed, indicates his abs, “…real?”

 

He chuckles, softly, and she realises what an absolutely moronic question that is – she can blame her proximity to his bare chest, right? Right.

 

“You should know,” she adds, firmly, “that normally I’m really smart.”

 

“I’ve heard that,” he agrees, seriously, and she smiles – he’s got that chest and those abs and that smile and he’s _nice_. God how gifted can one guy be? Well – Laurel had said he was nice. But Felicity hadn’t thought she’d really meant, you know… sweet, kind, funny.

 

“Can I…” she waves a hand, vaguely, but he steps into her personal space without needing to be asked and her fingers brush his bare skin and then she flinches back, automatically, swallowing.

 

“You,” Oliver’s voice is low and gentle and unbelievably sexy, all of a sudden, “can do whatever you want. You’re the boss.”

 

“Yes,” she agrees, after a moment, “yes, yup, yes I am.”

 

She pulls her knees up under her so she can kneel on the end of the bed, and lays her hand flat over one of his pecks – his skin is hot and the muscle is firm and… her mind goes entirely, inconveniently blank for a moment as she tries not to let her damn hand shake. (She’s the boss here, she needs to have some composure).

 

“Do you… I mean… how long did this…” she runs her fingers slowly down the centre of his chest, traces the outline of his six pack, feels, just for a moment, his breathing hitch.

 

“Do you really want to know?”

 

“Mm…” Felicity’s fingers reach the waistband of his boxers, which are tight enough that there isn’t much being left to the imagination there, either, not that she’s not curious… “no – nope – just – I talk a lot, I like talking, hate silence, me…”

 

She swallows, curls her fingers around the waistband of his boxers, glances up at his one raised eyebrow (is he cocky? Yeah, he’s a little cocky about this, isn’t he? Well fuck him she’s totally brave enough to do this).

She pushes the waistband of his boxers down, carefully, slowly exposing him. It does something white hot and tingly to her brain but she does it – Felicity Megan Smoak is now looking at naked male hooker penis and yes she has totally paid to look at it and everything but also she’s trying really hard not to hear her Bubbe turning her grave.

 

She does not want to think about Bubbe right now.

 

“Mmhm,” she mutters, “okay.”

 

“Okay?” Oliver asks, sounding more amused than is helpful right now, “should I be offended? Is that all you’ve got to say?”

 

“Well I’m told it’s not really the tool it’s what you do with it, so…”

 

Oliver throws his head back and laughs, and Felicity feels the full hysterical weight of this ridiculous situation she’s gotten herself into and giggles, too, glancing up at his face – he grins at her.

 

“Do you want to have sex with me, Felicity?” He asks, stepping out of his boxers, his smile still easy and warm, like they’re discussing what to have for dinner or where to go for lunch.

 

And the thing is that yes, yes, she kind of actually would now, wouldn’t she? Naked and grinning and kind of cocky and also nice, really nice and smelling really good. Felicity swallows. Time to be articulate and to the point, Miss Smoak. “I want you to go down on me.”

 

He shrugs, “okay. Anything else?”

 

“Mm – no. Not right now.”

 

“Okay.”

 

“Like this, though,” she adds, sitting again, “just like this – you – you kneel there. On the floor. And I’m here…”

 

“Okay, sure.”

 

And he gets on his knees, (oh fuck there’s a very naked very beautiful man kneeling on the floor between her legs oh – oh god), and gently pushes her skirt up her thighs. “Do you want to take your panties off, or not? I can work either way, up to you.”

 

“Mm no,” she shakes her head, “or – no, wait, I’m taking them off.”

 

He takes them off for her, gentle and professional – in fact he actually folds them (who folds panties, for god’s sake? She doesn’t even fold her panties!) and puts them neatly on the coverlet next to her.

 

“Okay?” He asks, as she settles comfortably above him – he’s stroking one of her calves and it feels kind of nice; she can feel the callouses on his fingertips.

 

“Mmhm. Yes. Okay – you can – you can start – ”

 

And okay, so it turns out that this man may be a _lot_ gifted.

 

Felicity Smoak has only ever dated three men – there was Barry, who was super adorable and sweet but also so clearly in love with someone else it had been kind of pointless. And before him Ray, which had been the single worst idea she’d ever had, protip: never date someone whose company you’re acquiring, because if you break up it will get squillions of dollars worth of ugly. And then of course before him there had been Cooper, who had turned out to be something of a criminally inclined cyber terrorist who Sara had had to drop kick off a roof.

 

So. Felicity doesn’t consider herself exactly inexperienced, it’s just that… she has never had time to date very much. Oliver will make the fourth man she’s ever had sexual relations with. She’s been growing and running her own company since her mid-teens and it’s rare that any man can manage to become more important to her than that. So she’s had sex, yes – oral sex – even quite good oral sex (bless him, Barry put a lot of effort in – to compensate for the whole, you know, being in love with someone else situation), but not anything like this. This… this is… officially a whole other level, seriously, wow – all the XP for Felicity Smoak.

 

She gasps, fastening a hand in Oliver’s hair, tensing –

 

“You okay?” He glances up at her, which is inconvenient because it means he’s stopped doing whatever he was doing with his tongue a moment ago.

 

“Mmhm – yeah – yup,” she swallows, hard, “no stopping, please.”

 

He grins at her. “You don’t have to say please.”

 

Then he goes back to work.

 

***  
  
Felicity Smoak, bless her, comes very, very easily (Oliver loves that in a client, really, he does). She was already kind of turned on by the whole situation – kind of obvious the moment he got a good look at her panties, she’d gotten wet just stroking his chest and taking his boxers off – and a man with his skills doesn’t need much more than that to get a woman off.

 

He doesn’t try to be hasty about it – she’s paying good money for his time, he’s not going to rush her – but really, truly, it doesn’t take much. He licks and teases her clit, she tries vainly not to moan and then throws dignity to the wind and makes some of the sweetest, sexiest noises he’s ever heard, squirming and whimpering and tugging his hair the whole damn time. He’s fairly sure that, at one point, she starts mumbling some kind of programming computer code – realises she’s trying to stop herself cumming and eases off a little until she’s merely blaspheming at him in English again – but that’s fucking adorable. He’s never made a woman do anything like that before.

 

And when he judges she’s gotten decent value for money, he pushes first one, then two fingers inside her and it’s all over – she yelps, high pitched and breathy, (“Oh – god – _fuck_ – ”) almost jerks all the way upright, then flops back onto her duvet again, tightening and spasming around his fingers once – twice – then she’s done.

 

He withdraws gently, carefully, sits back on his heels and wipes his mouth, listening to her breathing even out.

 

An hour, almost, of conversation to get her to… six, seven minutes of oral sex? Relatively easy job, all told, even if he had to tell her more about himself than he’s totally comfortable with.

 

And she’s fucking cute.

 

He stands up, looking down at her for a moment – she’s all hazy and dishevelled – she hasn’t taken her glasses off so they’re knocked half off her nose, one arm flung over her face, hair falling out of its pony tail, blouse coming open revealing that she’s not wearing a bra. The hint of her breast is more vulnerable than it is sexy, and he gently tugs her blouse closed for her, grabs one of her blankets and pulls it up over her, tucking a pillow under her head as she sighs and bonelessly acquiesces, yawning.

 

He kind of wishes he could have seen her a little more naked and wonders, just briefly, what actually having sex with her would be like. Not the kind she pays for – but what he thinks of, these days, as real sex, sex with someone where it isn’t a transaction – sex where it’s just them with no money involved and she’ll look him in the face afterwards. Sex where he could crawl into bed next to her now and smooth her hair and kiss her face until she was ready again – and then they would fuck, easily, messily, without performance or clinical detachment, until he could come groaning her name into her neck whilst she dug her heels into his back and kissed him and – but that’s a really dangerous line of thought to be indulging in right now.

 

“Hey, sweetheart,” he murmurs, and gently touches her arm, “you okay?”

 

“Mmhm,” she nods, not taking her arm off her face.

 

“You need anything else tonight?”

 

“Mm,” she shakes her head.

 

“Okay,” he keeps a hand on her shoulder, gentle, appreciative ( _tip me well_ , says that hand, _you know you want to_ ), “I’m gonna see myself out then, that alright?”

 

She nods, yawning.

 

“You need me again, you know how to reach me.”

 

“Mmhm.”

 

He gives her shoulder one last, gentle pat, then begins gathering his clothes, dresses quickly – he thinks she’s fallen asleep until he reaches her bedroom door and hears her murmur, “ _thank you_ ,” before he lets himself out.

 

“Any time, sweetheart.”

 

She smiles at him, dosily, from the bed, and he switches off her main light before he leaves.

 

Her terrifying bodyguard is sitting in the living room, playing cards with another woman – this one taller and darker and somehow even more dangerous looking than her companion. Felicity’s tablet, notebook and red pen are still discarded on the sofa next to them.

 

“You good?” The bodyguard raises an eyebrow at him as he passes.

 

“Yes, thanks, but I need to get home.”

 

“We can call you a car if you want,” she shrugs, “no problem.”

 

It’s that or two subway rides and a bus and he needs to get back before Thea wakes up to find him gone – “Okay.”

 

“Cool,” she pulls a phone from her pocket. “Your pay’s over there.”

 

She indicates an envelope on the counter. It feels reassuringly thick and weighty – Oliver gives its contents a brief check, then slips it into his briefcase, whilst the woman with the cards eyes him like she’s contemplating swallowing him.

 

His apartment, when he finally gets back to it, is dark and reassuringly quiet. He lets himself in, taking off his shoes so that he doesn’t set the floorboards in the hall creaking. He hides the briefcase on the very top shelf of the hall closet, behind the tins of old paint and cleaning supplies, although not before he’s pulled out the envelope.

 

Then he checks Thea’s bedroom door – still closed, no sign she’s been awake at all – and heads quietly to his own, where he tucks the envelope under his mattress (that’ll cover the washer-dryer nicely, he reckons, and the repair guy is coming tomorrow), and undresses again.

 

Just as he’s unbuttoning his shirt he thinks, unbidden, about the hand Felicity laid on his chest – about her slightly chewed nails and fine, delicate fingers and the way her eyelashes trembled as she glanced shyly up at him – remembers the trace of her fingertips skimming down his skin and the way she’d hesitated, touching the waistband of his boxers. She must have noticed him getting hard, right? She hadn’t meant to do that to him, he was fairly certain – just caught up in her own… stuff. But she’d looked right at him – she couldn’t exactly have failed to notice his semi.

 

Speaking of which…

 

Fuck, this is not a line of thought he should be having. You don’t fantasize about clients, for fuck’s sake – boundaries. Slippery slopes. All of that.

 

He brushes his teeth, glad to get the taste of her out of his throat. But his dick still has ideas of its own and that semi is not going to go away, is it? It’s five in the morning. He needs to be making Thea breakfast around eight or she won’t eat at all – he knows her – and he desperately needs to snatch a couple of hours of sleep so she doesn’t notice that he’s tired. He hasn’t had any sleep, really (he doesn’t sleep much at night these days, it’s why he was awake when Felicity called).

 

Fuck. Fuck it. He climbs into bed, carefully grasps himself, thinks of Felicity Smoak whimpering in html, and closes his eyes as he begins to stroke.

 


End file.
